Key West Vacation Rentals

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Search nearly 100 Key West vacation rentals ranging from intimate 2 bedroom cottages to large 6 bedroom homes. With properties in popular Key West communities like Truman Annex, Key West Golf Club, and 1800 Atlantic plus a variety of pet friendly and monthly rentals, we are sure we have the perfect fit for your trip. Our local Key West team of vacation rental experts has been helping travelers plan amazing vacations for decades and loves to share their local knowledge. Don't hesitate to contact us with questions or for help finding the perfect rental and booking your Key West vacation!

Displaying 37 - 48 of 89 rentals matching your search criteria
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Casa Grande

Type

  • Home
5 Bedrooms
5.5 Baths
12 Guests
Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!

4 Palms

Type

  • Condo
2 Bedrooms
2 Baths
6 Guests
Key West is all about the beach and the ocean! Located right by Smathers Beach, this tastefully decorated rental might just be the answer!

Perfect Pineapple

Type

  • Home
2 Bedrooms
1 Bath
4 Guests
Sit along side your private pool for morning coffee or your evening glass of wine.

The Hemingway

Type

  • Townhouse
2 Bedrooms
2 Baths
4 Guests
The location does not get better than this! Short bike ride to the beach and walking distance to most restaurants and shops!

Southard Getaway

Type

  • Condo
2 Bedrooms
1.5 Baths
5 Guests
“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree.

Coral Casita

Type

  • Townhouse
3 Bedrooms
3 Baths
8 Guests
Ideal for a family vacation or group of friends looking for a rental on a budget. Located very close to some great Key West restaurants this property is a steal!

Coral Palm

Type

  • Townhouse
3 Bedrooms
3 Baths
8 Guests
Completely remodeled, renovated and freshly painted 3 bedroom, 3 bath, 2 level Key West townhome is about to be your home away from home!

Verandah

Type

  • Home
2 Bedrooms
2.5 Baths
4 Guests
Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out.

Emma's Secret

Type

  • Condo
2 Bedrooms
1 Bath
4 Guests
Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.

Crowner's Jewel

Type

  • Townhouse
2 Bedrooms
2.5 Baths
6 Guests
Imagine being able to walk to the Sunset Celebrations every single evening! Only couple blocks to Mallory Square you can find this true gem!

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